Issue Emailing Single User Internally

I have one client who is having issues sending an internal email to one person at work, internally. Everyone else is able to email this person, and the perwson having the sending issues can send to everyone else. Any ideas? Runing Exchange 2010 w/ Outlook 2007 Client
TrihimbulusAsked:
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Alan HardistyConnect With a Mentor Co-OwnerCommented:
Have them pick the user from the Global Address List not from autocomplete and see if the problem stops.

If it does, delete the problem address from the autocomplete list.
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MegaNuk3Commented:
What NDR do they get?

Have you checked the 'Delivery Options' on the mailbox that user1 cannot send to? User1 might be listed as a blocked sender.
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TrihimbulusAuthor Commented:
Thye don't get an NDR - it just hangs in the Outbox and never goes anywhere. Everything is clean in Delivery Options
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MegaNuk3Commented:
What happens if user1 sends to user2 from OWA?
What happens if you turn off cached mode and repeat the above test on user1's machine?

Alan has a good point.

Also try outlook /safe on user1s machine and see if they can then email user2
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Auric1983Commented:
Also, you may want to have user 1 try sending the message to user 2 using OWA?
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pmorton23Commented:
have the user start a new email, then start to type the persons name in the TO field, when the name cache opens for suggestions, highlight the name in question and hit the delete button. it may be the incorrect email address is held in the name cache. even though you type in the email address it may resolve to an incorrect one stored on the local station. also try an email from owa or another station.
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